Hydrochloric Acid → HCID 71295285, compound

HRID 1776903Notes

Reaction equation

HRID 1776903 reaction equation
[NH2:1][C:2]1[C:23]([Br:24])=[CH:22][C:5]2[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=3[F:16])[O:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].Cl>ClCCl>[Br:24][C:23]1[C:2]([NH:1][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:3][C:4]2[O:8][C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=3[F:16])=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]=2[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 86728285HCID 86728285, compound

Product 1

HCID 71295285HCID 71295285, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 6-amino-5-bromo-2-(2,4-difluorophenyl)benzofuran-3-carboxylate (310 mg, 0.78 mmol) and pyridine (185 mg, 2.35 mmol) in dichloromethane (10 mL) was added dropwise methanesulfonyl chloride (179 mg, 1.56 mmol) at 0° C., then the mixture was stirred at 25° C. overnight. 10% HCl (aq) was added, then the mixture was extracted with dichloromethane (30 mL*3), dried over Na2SO4, and concentrated to provide ethyl 5-bromo-2-(2,4-difluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylate (350 mg, yield: 94%). 1H-NMR (CDCl3, 400 MHz) δ 8.32 (s, 1H), 7.91 (s, 1H), 7.64˜7.90 (m, 1H), 7.06 (d, J=3.0 Hz, 1H), 7.03 (d, J=3.0 Hz, 1H), 6.88 (s, 1H), 4.38 (q, J=7.2 Hz, 2H), 3.02 (s, 3H), 1.33 (t, J=7.6 Hz, 3H). MS (M+H)+: 474/476.

Workup

  1. extractionthe mixture was extracted with dichloromethane (30 mL*3)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9ab10053a61448f7a0a6d1f5668426d8
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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